ES2198130T3 - Catalizadores de cianuros metalicos dobles mejorados para fabricar polieter-poioles. - Google Patents

Catalizadores de cianuros metalicos dobles mejorados para fabricar polieter-poioles.

Info

Publication number: ES2198130T3
Authority: ES; Spain
Prior art keywords: catalyst; ethylene oxide; dmc; contain; polyether
Prior art date: 1998-03-10
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES99910277T

Other languages

English (en)

Spanish (es)

Inventor

Jorg Hofmann

Pieter Ooms

Pramod Gupta

Walter Schafer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-03-10

Filing date

1999-02-25

Publication date

2004-01-16

1999-02-25 Application filed by Bayer AG filed Critical Bayer AG

2004-01-16 Application granted granted Critical

2004-01-16 Publication of ES2198130T3 publication Critical patent/ES2198130T3/es

2019-02-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 116
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 title claims abstract description 12
238000004519 manufacturing process Methods 0.000 title claims description 36
229920000570 polyether Polymers 0.000 claims abstract description 72
239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 64
229910052751 metal Inorganic materials 0.000 claims abstract description 39
239000002184 metal Substances 0.000 claims abstract description 39
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 37
239000003446 ligand Substances 0.000 claims abstract description 29
-1 cyanide compound Chemical class 0.000 claims abstract description 18
229920005862 polyol Polymers 0.000 claims description 39
150000003077 polyols Chemical class 0.000 claims description 38
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 16
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
239000011701 zinc Substances 0.000 claims description 13
229910052725 zinc Inorganic materials 0.000 claims description 13
239000003999 initiator Substances 0.000 claims description 12
150000002825 nitriles Chemical class 0.000 claims description 10
239000007864 aqueous solution Substances 0.000 claims description 9
125000002947 alkylene group Chemical group 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
SZAVHWMCBDFDCM-KTTJZPQESA-N cobalt-60(3+);hexacyanide Chemical compound [60Co+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] SZAVHWMCBDFDCM-KTTJZPQESA-N 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
229920001400 block copolymer Polymers 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 2
239000000203 mixture Substances 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
229920001223 polyethylene glycol Polymers 0.000 description 11
230000000694 effects Effects 0.000 description 10
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
239000002202 Polyethylene glycol Substances 0.000 description 9
230000000052 comparative effect Effects 0.000 description 7
239000012153 distilled water Substances 0.000 description 7
238000001914 filtration Methods 0.000 description 7
229920001451 polypropylene glycol Polymers 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
229910017052 cobalt Inorganic materials 0.000 description 6
239000010941 cobalt Substances 0.000 description 6
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 6
230000006698 induction Effects 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
238000002411 thermogravimetry Methods 0.000 description 6
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
RKBAPHPQTADBIK-UHFFFAOYSA-N cobalt;hexacyanide Chemical compound [Co].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] RKBAPHPQTADBIK-UHFFFAOYSA-N 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
238000000605 extraction Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000011592 zinc chloride Substances 0.000 description 5
235000005074 zinc chloride Nutrition 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 3
239000004793 Polystyrene Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000013019 agitation Methods 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
150000004679 hydroxides Chemical class 0.000 description 3
229920002223 polystyrene Polymers 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
239000004814 polyurethane Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910001413 alkali metal ion Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001450 anions Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
150000001913 cyanates Chemical class 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000009413 insulation Methods 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
150000002540 isothiocyanates Chemical class 0.000 description 2
239000000178 monomer Substances 0.000 description 2
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
150000002823 nitrates Chemical class 0.000 description 2
150000003891 oxalate salts Chemical class 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000007151 ring opening polymerisation reaction Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
150000003567 thiocyanates Chemical class 0.000 description 2
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
229910021575 Iron(II) bromide Inorganic materials 0.000 description 1
229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
238000006887 Ullmann reaction Methods 0.000 description 1
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
125000005234 alkyl aluminium group Chemical group 0.000 description 1
238000010936 aqueous wash Methods 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
BWKDLDWUVLGWFC-UHFFFAOYSA-N calcium;azanide Chemical compound [NH2-].[NH2-].[Ca+2] BWKDLDWUVLGWFC-UHFFFAOYSA-N 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
INDBQWVYFLTCFF-UHFFFAOYSA-L cobalt(2+);dithiocyanate Chemical compound [Co+2].[S-]C#N.[S-]C#N INDBQWVYFLTCFF-UHFFFAOYSA-L 0.000 description 1
229940052810 complex b Drugs 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
238000002050 diffraction method Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
ZAEAYFVVHCPYDI-UHFFFAOYSA-N dizinc;iron(2+);hexacyanide Chemical compound [Fe+2].[Zn+2].[Zn+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] ZAEAYFVVHCPYDI-UHFFFAOYSA-N 0.000 description 1
UZZWBUYVTBPQIV-UHFFFAOYSA-N dme dimethoxyethane Chemical compound COCCOC.COCCOC UZZWBUYVTBPQIV-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 description 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
UETZVSHORCDDTH-UHFFFAOYSA-N iron(2+);hexacyanide Chemical compound [Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UETZVSHORCDDTH-UHFFFAOYSA-N 0.000 description 1
SWODCICMZQPBPU-UHFFFAOYSA-N iron(2+);nickel(2+);hexacyanide Chemical compound [Fe+2].[Ni+2].[Ni+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] SWODCICMZQPBPU-UHFFFAOYSA-N 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(II) nitrate Inorganic materials [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
GKWCCSUCDFFLBP-UHFFFAOYSA-N oxirane Chemical compound C1CO1.C1CO1 GKWCCSUCDFFLBP-UHFFFAOYSA-N 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
125000006353 oxyethylene group Chemical group 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
150000004707 phenolate Chemical class 0.000 description 1
229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
229920003251 poly(α-methylstyrene) Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000004904 shortening Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229910000018 strontium carbonate Inorganic materials 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000004763 sulfides Chemical class 0.000 description 1
AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000004246 zinc acetate Substances 0.000 description 1
229940102001 zinc bromide Drugs 0.000 description 1
JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
- B01J27/26—Cyanides
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Toxicology (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
General Health & Medical Sciences (AREA)
Polyethers (AREA)
Exhaust Gas Treatment By Means Of Catalyst (AREA)
Catalysts (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

ES99910277T 1998-03-10 1999-02-25 Catalizadores de cianuros metalicos dobles mejorados para fabricar polieter-poioles. Expired - Lifetime ES2198130T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19810269		1998-03-10
DE19810269A DE19810269A1 (de)	1998-03-10	1998-03-10	Verbesserte Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen

Publications (1)

Publication Number	Publication Date
ES2198130T3 true ES2198130T3 (es)	2004-01-16

Family

ID=7860352

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES99910277T Expired - Lifetime ES2198130T3 (es)	1998-03-10	1999-02-25	Catalizadores de cianuros metalicos dobles mejorados para fabricar polieter-poioles.

Country Status (17)

Country	Link
US (1)	US6291388B1 (de)
EP (1)	EP1071509B1 (de)
JP (1)	JP2002506088A (de)
KR (1)	KR100561570B1 (de)
CN (1)	CN1137780C (de)
AT (1)	ATE239548T1 (de)
AU (1)	AU2929199A (de)
BR (1)	BR9908594A (de)
CA (1)	CA2322823C (de)
DE (2)	DE19810269A1 (de)
DK (1)	DK1071509T3 (de)
ES (1)	ES2198130T3 (de)
HU (1)	HUP0105448A3 (de)
ID (1)	ID25618A (de)
PT (1)	PT1071509E (de)
TW (1)	TW541205B (de)
WO (1)	WO1999046042A1 (de)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19817676A1 (de)	1998-04-21	1999-10-28	Bayer Ag	Verfahren zur aufarbeitungsfreien Herstellung langkettiger Polyetherpolyole
DE19905611A1 (de) *	1999-02-11	2000-08-17	Bayer Ag	Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen
DE19918727A1 (de)	1999-04-24	2000-10-26	Bayer Ag	Langkettige Polyetherpolyole mit hohem Anteil primärer OH-Gruppen
DE19928156A1 (de)	1999-06-19	2000-12-28	Bayer Ag	Aus Polyetherpolyolen hergestellte Polyurethan-Weichschäume
DE19953546A1 (de)	1999-11-08	2001-05-10	Bayer Ag	Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen
US6642171B2 (en)	2000-04-28	2003-11-04	Synuthane International, Inc.	Double metal cyanide catalysts containing polyglycol ether complexing agents
DE10108484A1 (de)	2001-02-22	2002-09-05	Bayer Ag	Verbessertes Verfahren zur Herstelung von Polyetherpolyolen
DE10108485A1 (de)	2001-02-22	2002-09-05	Bayer Ag	Verbessertes Verfahren zur Herstellung von Polyetherpolyolen
JP2005520892A (ja) *	2002-03-21	2005-07-14	ダウグローバルテクノロジーズインコーポレイティド	部分混和性錯化剤を用いる金属シアニド触媒の製造方法
US7157549B2 (en) *	2003-05-30	2007-01-02	The University Of Akron	Polymerization of oxiranes with a lithium-containing initiator
CN1308078C (zh) *	2004-11-29	2007-04-04	黎明化工研究院	六氰钴锰氰化物络合物催化剂及其制备方法和用途
US8093351B2 (en)	2006-08-24	2012-01-10	Cornell Research Foundation, Inc.	Copolymerization of propylene oxide and carbon dioxide and homopolymerization of propylene oxide
KR101404702B1 (ko)	2011-03-08	2014-06-17	에스케이이노베이션 주식회사	에테르 결합 단위체를 함유한 이산화탄소/에폭사이드 공중합체의 제조 방법
SG11201402998PA (en)	2011-12-20	2014-10-30	Bayer Ip Gmbh	Hydroxy-aminopolymers and method for producing same
US9562134B2 (en)	2013-03-12	2017-02-07	Covestro Llc	Catalyst for the production of polyols having lower amounts of high molecular weight tail
GB201515350D0 (en)	2015-08-28	2015-10-14	Econic Technologies Ltd	Method for preparing polyols
GB201703324D0 (en)	2017-03-01	2017-04-12	Econic Tech Ltd	Method for preparing polyether carbonates
GB201717441D0 (en)	2017-10-24	2017-12-06	Econic Tech Ltd	A polymerisation process
WO2019209348A1 (en)	2018-04-28	2019-10-31	Liang Wang	Polyurethane elastomer with high ultimate elongation
GB201814526D0 (en)	2018-09-06	2018-10-24	Econic Tech Ltd	Methods for forming polycarbonate ether polyols and high molecular weight polyether carbonates
GB201906210D0 (en)	2019-05-02	2019-06-19	Econic Tech Limited	A polyol block copolymer, compositions and processes therefor
GB201906214D0 (en)	2019-05-02	2019-06-19	Econic Tech Ltd	A polyol block copolymer, compositions and processes therefor
GB202003002D0 (en)	2020-03-02	2020-04-15	Crane Ltd	Method of preparation of a polyol block copolymer
GB202003003D0 (en)	2020-03-02	2020-04-15	Econic Tech Ltd	A polyol block copolymer
GB202017531D0 (en)	2020-11-05	2020-12-23	Econic Tech Limited	(poly)ol block copolymer
KR20240036722A (ko)	2021-08-11	2024-03-20	에코닉 테크놀로지 엘티디	거대고리형 이원금속 촉매 및 이중 금속 시아나이드 촉매의 혼합물을 사용한 에폭사이드 및 co2의 공중합에 의한 계면활성제 제조 방법
GB202115335D0 (en)	2021-10-25	2021-12-08	Econic Tech Ltd	Surface-active agent
US20250109246A1 (en)	2021-12-16	2025-04-03	Dow Global Technologies Llc	Novel nonionic surfactants and processes to make them
EP4302874A1 (de)	2022-07-04	2024-01-10	Covestro Deutschland AG	Verfahren zur herstellung von doppelmetallcyanid-katalysatoren
GB2626546A (en)	2023-01-25	2024-07-31	Econic Tech Ltd	Surface-active agent
GB2626989A (en)	2023-02-10	2024-08-14	Econic Tech Ltd	Surface-active agent
GB2629367A (en)	2023-04-25	2024-10-30	Econic Tech Ltd	Surface-active agent
EP4702078A1 (de)	2023-04-25	2026-03-04	Unilever IP Holdings B.V.	Zusammensetzungen
WO2025051643A1 (de)	2023-09-05	2025-03-13	Covestro Deutschland Ag	Verfahren zur herstellung von doppelmetallcyanid-katalysatoren
EP4520431A1 (de)	2023-09-05	2025-03-12	Covestro Deutschland AG	Verfahren zur herstellung von doppelmetallcyanid-katalysatoren
JP7751714B1 (ja) *	2024-11-18	2025-10-08	Ａｇｃ株式会社	複合金属シアン化物錯体触媒粉末及びポリエーテル化合物の製造方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1063525A (en)	1963-02-14	1967-03-30	Gen Tire & Rubber Co	Organic cyclic oxide polymers, their preparation and tires prepared therefrom
US3829505A (en)	1970-02-24	1974-08-13	Gen Tire & Rubber Co	Polyethers and method for making the same
US3941849A (en)	1972-07-07	1976-03-02	The General Tire & Rubber Company	Polyethers and method for making the same
US5158922A (en)	1992-02-04	1992-10-27	Arco Chemical Technology, L.P.	Process for preparing metal cyanide complex catalyst
US5482908A (en) *	1994-09-08	1996-01-09	Arco Chemical Technology, L.P.	Highly active double metal cyanide catalysts
US5545601A (en)	1995-08-22	1996-08-13	Arco Chemical Technology, L.P.	Polyether-containing double metal cyanide catalysts
US5627120A (en) *	1996-04-19	1997-05-06	Arco Chemical Technology, L.P.	Highly active double metal cyanide catalysts

1998
- 1998-03-10 DE DE19810269A patent/DE19810269A1/de not_active Withdrawn
1999
- 1999-02-25 WO PCT/EP1999/001203 patent/WO1999046042A1/de not_active Ceased
- 1999-02-25 CN CNB998038016A patent/CN1137780C/zh not_active Expired - Lifetime
- 1999-02-25 EP EP99910277A patent/EP1071509B1/de not_active Expired - Lifetime
- 1999-02-25 AT AT99910277T patent/ATE239548T1/de not_active IP Right Cessation
- 1999-02-25 DE DE59905468T patent/DE59905468D1/de not_active Expired - Lifetime
- 1999-02-25 PT PT99910277T patent/PT1071509E/pt unknown
- 1999-02-25 HU HU0105448A patent/HUP0105448A3/hu unknown
- 1999-02-25 ID IDW20001716A patent/ID25618A/id unknown
- 1999-02-25 BR BR9908594-1A patent/BR9908594A/pt not_active Application Discontinuation
- 1999-02-25 JP JP2000535449A patent/JP2002506088A/ja active Pending
- 1999-02-25 AU AU29291/99A patent/AU2929199A/en not_active Abandoned
- 1999-02-25 US US09/623,648 patent/US6291388B1/en not_active Expired - Lifetime
- 1999-02-25 DK DK99910277T patent/DK1071509T3/da active
- 1999-02-25 KR KR1020007009947A patent/KR100561570B1/ko not_active Expired - Lifetime
- 1999-02-25 CA CA002322823A patent/CA2322823C/en not_active Expired - Fee Related
- 1999-02-25 ES ES99910277T patent/ES2198130T3/es not_active Expired - Lifetime
- 1999-03-08 TW TW088103494A patent/TW541205B/zh active

Also Published As

Publication number	Publication date
DK1071509T3 (da)	2003-09-01
DE59905468D1 (de)	2003-06-12
DE19810269A1 (de)	2000-05-11
TW541205B (en)	2003-07-11
AU2929199A (en)	1999-09-27
BR9908594A (pt)	2000-11-14
CN1292727A (zh)	2001-04-25
PT1071509E (pt)	2003-09-30
WO1999046042A1 (de)	1999-09-16
KR20010041718A (ko)	2001-05-25
US6291388B1 (en)	2001-09-18
ID25618A (id)	2000-10-19
KR100561570B1 (ko)	2006-03-16
HUP0105448A3 (en)	2003-08-28
ATE239548T1 (de)	2003-05-15
CA2322823C (en)	2007-08-07
HK1036024A1 (en)	2001-12-21
HUP0105448A2 (hu)	2002-04-29
JP2002506088A (ja)	2002-02-26
CN1137780C (zh)	2004-02-11
EP1071509A1 (de)	2001-01-31
EP1071509B1 (de)	2003-05-07
CA2322823A1 (en)	1999-09-16

Publication	Publication Date	Title
ES2198130T3 (es)	2004-01-16	Catalizadores de cianuros metalicos dobles mejorados para fabricar polieter-poioles.
ES2201537T3 (es)	2004-03-16	Catalizadores cristalinos de cianuros metalicos dobles para la fabricacion de polioles polieter.
ES2217807T3 (es)	2004-11-01	Catalizadores de cianuro bimetalico para la preparacion de polioleteres.
US5545601A (en)	1996-08-13	Polyether-containing double metal cyanide catalysts
AU702299B2 (en)	1999-02-18	Highly active double metal cyanide complex catalysts
US5693584A (en)	1997-12-02	Highly active double metal cyanide catalysts
ES2230882T3 (es)	2005-05-01	Catalizadores de cianuro bimetalico para la preparacion de polioleteres.
ES2240194T3 (es)	2005-10-16	Catalizadores de cianuro bimetalico para la preparacion de polioleteres.
ES2199712T3 (es)	2004-03-01	Nuevos catalizadores de cianuro bimetalico para la fabricacion de polioleteres.
EP1515801B1 (de)	2005-10-26	Herstellung eines doppelmetallcyanidkatalysators
KR100563505B1 (ko)	2006-03-23	칼슘 화합물로 개질된 이중 금속 시아니드 착체 촉매
KR19990087364A (ko)	1999-12-27	고활성 이중 금속 시아나이드 촉매
KR20080067971A (ko)	2008-07-22	폴리에테르 폴리올의 제조를 위한 이중 금속 시안화물 촉매
EP1529566A1 (de)	2005-05-11	Ungesättigte tertiäre Alkohole als Liganden für aktive DMC-Katalysatoren
ES2219048T3 (es)	2004-11-16	Catalizadores de cianuro bimetalico para la preparacion de polioleteres.
ES2207002T3 (es)	2004-05-16	Catalizador cristalinos de cianuro bimetalico que contienen poliester para la fabricacion de polieter-polioles.
ES2207029T3 (es)	2004-05-16	Catalizadores de cianuro bimetalico para la preparacion de polioleteres.
MXPA03006392A (es)	2005-08-16	Mezclas iniciadoras activadas y los procedimientos con ellas relacionados.
ES2233372T3 (es)	2005-06-16	Catalizadores de cianuro bimetalico para la fabricacion de polieterpolioles.
ES2219309T3 (es)	2004-12-01	Procedimiento para la obtencion de polieterpolioles.
ES2219059T3 (es)	2004-11-16	Catalizadores de cianuros bimetalicos para la preparacion de polioleteres.
EP1634644A1 (de)	2006-03-15	Herstellungsverfahren von Doppelmetallcyanidkatalysatoren (DMC Katalysatoren)
ES2242872T3 (es)	2005-11-16	Catalizadores de cianuro bimetalico para la preparacion de polioleteres.
MXPA00008727A (en)	2001-07-31	Improved double metal cyanide catalysts for producing polyether polyols
KR100908351B1 (ko)	2009-07-20	랜덤 폴리올 제조용 복금속 시안계 촉매